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Top Rated

Loved by recent travelers

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One of our most booked experiences

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Up to 24 hours before the experience starts

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Find your best option

Choose your package

Select an option to see its live dates and timings.

Highlights

  • Spend 2.5 hours sailing on the River or Lake with dinner included.
  • Enjoy the climate-controlled deck while watching the skyline pass by.
  • Taste chef-prepared food with panoramic city views during the ride.
  • Add drinks from the bar to complete your special evening out.
  • Pick a plated menu or buffet depending on your cruise route.

Your Experience

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Board a vessel that glides past major landmarks under the evening sky. The trip lasts roughly two and a half hours from start to finish.

Dining Options

You may select a plated meal featuring American flavors or a buffet with global dishes. Menus vary by route and can be reviewed before you book.

Views and Entertainment

Large windows offer clear sightlines to illuminated skyscrapers and bridges. A DJ or live performer keeps the atmosphere lively while you eat.

Comfort and Needs

The interior remains temperature controlled for a pleasant experience regardless of weather. Staff will try to meet specific dietary needs when notified in advance.

Inclusions & Exclusions

  • 2.5-hour cruise with dinner on the Chicago River or Lake Michigan.
  • Plated dinner with modern American cuisine ( Menu ) (<a href="https://cdn-imgix.headout.com/media/pdfs/6df77365ff708b1cd21aa9e53a88d6ce-OdysseyChicagoRiverArchitectureDinnerCruiseMenu.pdf">here</a>) (<a href="https://cdn-imgix.headout.com/media/pdfs/9348619257882f0c45bce89f9f242106-OdysseyLakeMichiganDinnerCruise_Menu.pdf">here</a>)
  • Plated 3-course meal with contemporary American food ( Menu )
  • Buffet dinner with global fusion items ( Menu ) (<a href="https://cdn-imgix.headout.com/media/pdfs/fe5e17b0f05963bd74f8d41e7de39d1c-LakeMichiganDinnerCruiseMenu.pdf">here</a>)
  • Sightseeing views of the skyline at twilight.
  • Live entertainment during the trip.
  • Access to the climate-controlled indoor area.
  • Efforts to accommodate dietary needs.
  • Bar service for cocktails, wine, and beer (extra cost).
  • Alcoholic beverages purchased on board.
  • Transport to or from the departure point.
  • Personal purchases made during the trip.

This product offers multiple ticket options. Some items above (like transfers or fast-track access) may only apply to specific options — confirm what's included when you select yours.

Must Know

  • Guests over 21 need ID for bar access.
  • Arrive 45 minutes early for check-in.
  • Boarding starts 30 mins prior on weekdays.
  • Boarding starts 45 mins prior on Sundays.
  • Bring a jacket for the outdoor deck.
  • No outside food, drinks, or weapons allowed.

Ticket Delivery

  • Your voucher will be emailed to you shortly.
  • Display the voucher on your mobile phone with a valid photo ID at the starting point.
  • Please check your final voucher for the starting point details & specific instructions.

Cancellation Policy

Free cancellation up to 24 hours before the experience starts.

Frequently asked questions

Clear answers to the most common questions travelers ask before booking this experience.

Booking FAQs

A valid ID is required for guests aged 21 and above to access the onboard bar. It’s recommended to carry a light jacket or wrap, as the open-air deck can get breezy.

Bringing outside food or beverages on board is not permitted. Weapons of any kind are strictly prohibited on the cruise.

Boarding begins 30 minutes prior to departure from Monday to Saturday, and 45 minutes before departure on Sundays. Guests should arrive at least 45 minutes early for check-in and boarding, and allow an additional 30 minutes for parking and reaching the boarding location. Cruise timings may vary, so refer to the cruise calendar and your email confirmation for the most accurate schedule. This is a seasonal experience and may be affected by weather conditions. Menu offerings are subject to change depending on seasonal availability.

You will require a ticket to participate in this cruise, which includes a sightseeing and dinner experience on either the Chicago River or Lake Michigan.

Yes, mandatory security checks are conducted prior to boarding. Skip-the-line benefits do not apply to these required procedures.

The cruise offers twilight views of the Chicago skyline and live entertainment onboard as part of its highlights.

Yes, guests aged 21 and above must present a valid ID to access the onboard bar. It's recommended to carry one even if you don't plan on using it.

It is advised to bring a light jacket or wrap, as the open-air deck can be breezy during your cruise experience.

Outside food and beverages are not permitted on board. Additionally, weapons of any kind are strictly prohibited.

You can choose between a plated gourmet dinner with modern American cuisine, a plated three-course meal with contemporary American dishes, or a buffet featuring global fusion cuisine. The specific menu depends on your selected option.

Boarding begins 30 minutes prior to departure from Monday to Saturday and 45 minutes before departure on Sundays, so plan accordingly to ensure timely boarding.

Alcoholic beverages are available for purchase onboard but are not included with your cruise ticket. Other additional purchases made during the trip will also incur extra charges.

No, transportation to and from the departure point is not covered by your cruise ticket. You'll need to arrange this separately.

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